1,1'-di-(4'-fluorophenyl)-tetramethyldisilane

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,1'-di-(4'-fluorophenyl)-tetramethyldisilane
• 英文别名: (4-Fluorophenyl)-[(4-fluorophenyl)-dimethylsilyl]-dimethylsilane
• 化学式: C₁₆H₂₀F₂Si₂
• 分子量: 306.503
• InChiKey: UBMWHERDEBZWAY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.57
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  乙酸肉桂酯 、 1,1'-di-(4'-fluorophenyl)-tetramethyldisilane 在 lithium chloride 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以98%的产率得到(4-fluorophenyl)-dimethyl-[(E)-3-phenylprop-2-enyl]silane
  参考文献：
  名称：

  Silylation of Allylic Trifluoroacetates and Acetates Using Organodisilanes Catalyzed by Palladium Complex

  摘要：

  Silylation of allylic acetates (1) using organodisilanes (2) was carried out in the presence of a catalytic amount of Pd(DBA)2-LiCl at 100 degrees C. The silylation proceeded smoothly without beta-hydrogen elimination of. resulting (pi-allyl)palladium intermediate. The added chloride salt such as LiCl or NaCl was indispensable for the catalytic activity. On the other hand, remarkable improvement of the silylation was realized by employing allylic trifluoroacetates (4) in place of the acetates (1) as the substrates. The silylation proceeded even at room temperature, and the added chloride salts was not necessary as the catalyst component. In the silylation, transmetalation of the disilanes (2) with (eta(3)-allyl)palladium intermediate (7) might be a critical step in the catalytic cycle. Model reactions for the transmetalation were carried out.

  DOI：

  10.1021/jo960345t
• 作为产物：
  描述：

  (p-Fluor-phenyl)-dimethyl-chlor-silan 在 四丁基高氯酸铵 作用下， 以 四氢呋喃 为溶剂， 以76 %的产率得到1,1'-di-(4'-fluorophenyl)-tetramethyldisilane
  参考文献：
  名称：

  从氯硅烷合成乙硅烷和低聚硅烷的电化学策略**

  摘要：

  Si−Si键的形成是有机合成中的一个重要转变。在此，我们提出了一种统一的电化学策略，用于从容易获得的氯硅烷中高效、选择性地合成乙硅烷、低聚硅烷和环硅烷——它们是合成功能性有机化合物和聚合化合物的重要前体。

  DOI：

  10.1002/anie.202303592

文献信息

• Palladium-catalyzed decarbonylative coupling of acid chlorides, organodisilanes, and 1,3-dienes
  作者：Yasushi Obora、Yasushi Tsuji、Takashi Kawamura

  DOI：10.1021/ja00075a089

  日期：1993.11
• 1,4-Carbosilylation of 1,3-Dienes via Palladium Catalyzed Three-Component Coupling Reaction
  作者：Yasushi Obora、Yasushi Tsuji、Takashi Kawamura

  DOI：10.1021/ja00144a005

  日期：1995.10

  Three-component coupling reaction of acid chlorides, organodisilanes, and 1,3-dienes achieves 1,4-carbosilylation of the 1,3-dienes to afford allylic silanes as the product. Bis(dibenzylideneacetone)palladium, a naked Pd(0) complex without donating ligand, showed high catalytic activity. A carbon and a silicon substituent are introduced at 1- and 4-positions of the 1,3-dienes regio- and stereoselectively with concomitant decarbonylation of the acid chlorides. A wide variety of allylic silanes are synthesized in high yields from these easily accessible substrates. On the other hand, a bully acid chloride such as adamantane-1-carboxylic acid chloride did not undergo the decarbonylation reaction but afforded allylic silanes containing acyl functionality. In all these reactions, transmetalation of the disilanes with eta(3)-allylchloropalladium intermediates might be a critical step in the catalytic cycle. As a model reaction for the transmetalation, reaction of di-mu-chlorobis[(1,2,3-eta)-4-phenyl-2-butenyl]dipalladium with disilanes was carried out. Although intermediate eta(3)-allylsilylpalladium species could not be detected, the corresponding allylic silanes, silyl chlorides, and Pd(0) metal were formed during the reaction. Furthermore, a similar three-component coupling reaction using aryl iodides, organosilylstannanes, and dienes also proceeded. However, the selectivity and the yield decreased considerably.
• Silylation of Allylic Trifluoroacetates and Acetates Using Organodisilanes Catalyzed by Palladium Complex
  作者：Yasushi Tsuji、Masahiro Funato、Masakatsu Ozawa、Hiroaki Ogiyama、Satoshi Kajita、Takashi Kawamura

  DOI：10.1021/jo960345t

  日期：1996.1.1

  Silylation of allylic acetates (1) using organodisilanes (2) was carried out in the presence of a catalytic amount of Pd(DBA)2-LiCl at 100 degrees C. The silylation proceeded smoothly without beta-hydrogen elimination of. resulting (pi-allyl)palladium intermediate. The added chloride salt such as LiCl or NaCl was indispensable for the catalytic activity. On the other hand, remarkable improvement of the silylation was realized by employing allylic trifluoroacetates (4) in place of the acetates (1) as the substrates. The silylation proceeded even at room temperature, and the added chloride salts was not necessary as the catalyst component. In the silylation, transmetalation of the disilanes (2) with (eta(3)-allyl)palladium intermediate (7) might be a critical step in the catalytic cycle. Model reactions for the transmetalation were carried out.
• An Electrochemical Strategy to Synthesize Disilanes and Oligosilanes from Chlorosilanes**
  作者：Weiyang Guan、Lingxiang Lu、Qifeng Jiang、Alexandra F. Gittens、Yi Wang、Luiz F. T. Novaes、Rebekka S. Klausen、Song Lin

  DOI：10.1002/anie.202303592

  日期：2023.6.26

  Si−Si bonds is an important transformation in organic synthesis. Herein, we present a unified electrochemical strategy for the efficient and selective synthesis of disilanes, oligosilanes, and cyclosilanes—which are important precursors for the synthesis of functional organic and polymeric compounds—from readily available chlorosilanes.

  Si−Si键的形成是有机合成中的一个重要转变。在此，我们提出了一种统一的电化学策略，用于从容易获得的氯硅烷中高效、选择性地合成乙硅烷、低聚硅烷和环硅烷——它们是合成功能性有机化合物和聚合化合物的重要前体。